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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015197

Secondary Accession Numbers

HMDB15197

Metabolite Identification

Common Name

Isoproterenol

Description

Isoproterenol is only found in individuals that have used or taken this drug. It is an isopropyl analog of epinephrine; beta-sympathomimetic that acts on the heart, bronchi, skeletal muscle, alimentary tract, etc. It is used mainly as bronchodilator and heart stimulant. [PubChem]The pharmacologic effects of isoproterenol are at least in part attributable to stimulation through beta-adrenergic receptors of intracellular adenyl cyclase, the enzyme that catalyzes the conversion of adenosine triphosphate (ATP) to cyclic AMP. Increased cyclic AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0254048
     RDKit          3D
LEVISOPRENALINE
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.6929    0.3785    1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3954   -0.3832   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5360    0.4929   -1.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1343   -1.0209   -0.0214 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9955   -0.1587    0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2206   -1.0612    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2624   -1.8072   -0.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884   -0.2665    0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366    1.0751    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7561    1.7532    0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9183    1.0830    0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1459    1.7266    0.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.2725   -0.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0866   -0.9295   -0.4363 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790   -0.8917   -0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4020   -0.3018    1.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701    0.6183    1.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0365    1.2551    1.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1769   -1.1772   -0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711    1.4467   -1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1700   -0.0864   -2.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6056    0.6976   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -1.8393    0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8813    0.4245   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    0.5023    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2201   -1.6963    1.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2969   -2.7782   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    1.5996    0.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8340    2.8083    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3055    2.6905    0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0006   -1.9216   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6414   -1.9600   -0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
M  END

1064
  Mrv0541 02231215132D          

 15 15  0  0  1  0            999 V2000
    2.8075    0.9529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -1.9347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.7597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.7779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    3.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2 13  1  0  0  0  0
  3 15  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015197

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)NCC(O)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3

> <INCHI_KEY>
JWZZKOKVBUJMES-UHFFFAOYSA-N

> <FORMULA>
C11H17NO3

> <MOLECULAR_WEIGHT>
211.2576

> <EXACT_MASS>
211.120843415

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
23.040744198970902

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
0.24020568214781188

> <ALOGPS_LOGS>
-1.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.65298229511258

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.814518857707053

> <JCHEM_PKA_STRONGEST_BASIC>
8.960251879660621

> <JCHEM_POLAR_SURFACE_AREA>
72.72

> <JCHEM_REFRACTIVITY>
58.39770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoproterenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254048
     RDKit          3D
LEVISOPRENALINE
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.6929    0.3785    1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3954   -0.3832   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5360    0.4929   -1.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1343   -1.0209   -0.0214 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9955   -0.1587    0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2206   -1.0612    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2624   -1.8072   -0.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884   -0.2665    0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366    1.0751    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7561    1.7532    0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9183    1.0830    0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1459    1.7266    0.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.2725   -0.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0866   -0.9295   -0.4363 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790   -0.8917   -0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4020   -0.3018    1.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701    0.6183    1.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0365    1.2551    1.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1769   -1.1772   -0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711    1.4467   -1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1700   -0.0864   -2.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6056    0.6976   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -1.8393    0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8813    0.4245   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    0.5023    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2201   -1.6963    1.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2969   -2.7782   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    1.5996    0.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8340    2.8083    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3055    2.6905    0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0006   -1.9216   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6414   -1.9600   -0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1064                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.241   1.779   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.907  -3.611   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.574  -5.151   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.908   3.319   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.574   1.009   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.908   1.779   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.242   4.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.574  -0.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.242   5.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.576   3.319   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.241  -1.301   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.908  -1.301   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.241  -2.841   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908  -2.841   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.574  -3.611   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2   13                                                            
CONECT    3   15                                                            
CONECT    4    6    7                                                       
CONECT    5    1    6    8                                                  
CONECT    6    4    5                                                       
CONECT    7    4    9   10                                                  
CONECT    8    5   11   12                                                  
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    8   13                                                       
CONECT   12    8   14                                                       
CONECT   13    2   11   15                                                  
CONECT   14   12   15                                                       
CONECT   15    3   13   14                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0015197
HETATM    1  C1  UNL     1      -3.443   1.383  -0.245  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.256  -0.102  -0.449  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.523  -0.740   0.143  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.134  -0.569   0.284  1.00  0.00           N  
HETATM    5  C4  UNL     1      -0.852  -0.024  -0.099  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.162  -0.697   0.800  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.137  -0.407   2.111  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.549  -0.395   0.477  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.515  -0.800   1.387  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.856  -0.568   1.178  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.281   0.090   0.031  1.00  0.00           C  
HETATM   12  O2  UNL     1       5.618   0.316  -0.167  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.336   0.496  -0.876  1.00  0.00           C  
HETATM   14  O3  UNL     1       3.696   1.154  -2.036  1.00  0.00           O  
HETATM   15  C11 UNL     1       1.996   0.250  -0.642  1.00  0.00           C  
HETATM   16  H1  UNL     1      -3.959   1.536   0.737  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.209   1.684  -1.020  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.518   1.943  -0.337  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.215  -0.361  -1.536  1.00  0.00           H  
HETATM   20  H5  UNL     1      -4.650  -0.368   1.179  1.00  0.00           H  
HETATM   21  H6  UNL     1      -5.401  -0.459  -0.449  1.00  0.00           H  
HETATM   22  H7  UNL     1      -4.311  -1.838   0.145  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.054  -1.618   0.144  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.626  -0.176  -1.173  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.761   1.077   0.115  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.012  -1.802   0.631  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.204   0.469   2.402  1.00  0.00           H  
HETATM   28  H13 UNL     1       2.242  -1.322   2.306  1.00  0.00           H  
HETATM   29  H14 UNL     1       4.623  -0.873   1.870  1.00  0.00           H  
HETATM   30  H15 UNL     1       6.044   0.779  -0.953  1.00  0.00           H  
HETATM   31  H16 UNL     1       4.643   1.369  -2.277  1.00  0.00           H  
HETATM   32  H17 UNL     1       1.273   0.573  -1.361  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4   19
CONECT    3   20   21   22
CONECT    4    5   23
CONECT    5    6   24   25
CONECT    6    7    8   26
CONECT    7   27
CONECT    8    9    9   15
CONECT    9   10   28
CONECT   10   11   11   29
CONECT   11   12   13
CONECT   12   30
CONECT   13   14   15   15
CONECT   14   31
CONECT   15   32
END

HMDB0254048
     RDKit          3D
LEVISOPRENALINE
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.6929    0.3785    1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3954   -0.3832   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5360    0.4929   -1.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1343   -1.0209   -0.0214 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9955   -0.1587    0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2206   -1.0612    0.2333 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2624   -1.8072   -0.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884   -0.2665    0.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366    1.0751    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7561    1.7532    0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9183    1.0830    0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1459    1.7266    0.1705 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.2725   -0.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0866   -0.9295   -0.4363 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790   -0.8917   -0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4020   -0.3018    1.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701    0.6183    1.2266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0365    1.2551    1.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1769   -1.1772   -0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711    1.4467   -1.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1700   -0.0864   -2.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6056    0.6976   -1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -1.8393    0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8813    0.4245   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    0.5023    1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2201   -1.6963    1.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2969   -2.7782   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    1.5996    0.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8340    2.8083    0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3055    2.6905    0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0006   -1.9216   -0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6414   -1.9600   -0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+-)-Isoprenaline	ChEBI
(+-)-Isoproterenol	ChEBI
1-(3,4-Dihydroxyphenyl)-2-(isopropylamino)ethanol	ChEBI
1-(3,4-Dihydroxyphenyl)-2-isopropylaminoethanol	ChEBI
3,4-Dihydroxy-alpha-[(isopropylamino)methyl]benzyl alcohol	ChEBI
alpha-(Isopropylaminomethyl)protocatechuyl alcohol	ChEBI
Isoprenalina	ChEBI
Isoprenalinum	ChEBI
Isopropyl noradrenaline	ChEBI
N-Isopropyl-beta-dihydroxyphenyl-beta-hydroxyethylamine	ChEBI
N-Isopropylnoradrenaline	ChEBI
N-Isopropylnorepinephrine	ChEBI
Isoprenaline	Kegg
3,4-Dihydroxy-a-[(isopropylamino)methyl]benzyl alcohol	Generator
3,4-Dihydroxy-α-[(isopropylamino)methyl]benzyl alcohol	Generator
a-(Isopropylaminomethyl)protocatechuyl alcohol	Generator
Α-(isopropylaminomethyl)protocatechuyl alcohol	Generator
N-Isopropyl-b-dihydroxyphenyl-b-hydroxyethylamine	Generator
N-Isopropyl-β-dihydroxyphenyl-β-hydroxyethylamine	Generator
Epinephrine isopropyl homolog	HMDB
Isoprenalin	HMDB
Isopropydrin	HMDB
Isopropyladrenaline	HMDB
Isopropylarterenol	HMDB
Isopropylnoradrenaline	HMDB
Isopropylnorepinephrine	HMDB
Isoproterenol chloride	HMDB
L-Isopropylnoradrenaline	HMDB
L-Isoproterenol	HMDB
Euspiran	HMDB
Isuprel	HMDB
Isadrin	HMDB
4-(1-Hydroxy-2-((1-methylethyl)amino)ethyl)-1,2-benzenediol	HMDB
Norisodrine	HMDB
Hydrochloride, isoproterenol	HMDB
Isadrine	HMDB
Isoproterenol hydrochloride	HMDB
Isoproterenol sulfate	HMDB
Izadrin	HMDB
Noradrenaline, isopropyl	HMDB
Novodrin	HMDB
Sulfate, isoproterenol	HMDB
Isoproterenol	ChEBI

Chemical Formula

C₁₁H₁₇NO₃

Average Molecular Weight

211.2576

Monoisotopic Molecular Weight

211.120843415

IUPAC Name

4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol

Traditional Name

isoproterenol

CAS Registry Number

7683-59-2

SMILES

CC(C)NCC(O)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3

InChI Key

JWZZKOKVBUJMES-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Secondary amine
Secondary aliphatic amine
Aromatic alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:64317 )
catechols (CHEBI:64317 )
secondary amino compound (CHEBI:64317 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015197)
Membrane (HMDB: HMDB0015197)

Source

Exogenous

Exogenous (HMDB: HMDB0015197)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Isoprenaline Action Pathway (PathBank: SMP0000663)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	170.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5.86 g/L	Not Available
LogP	1.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	149.44	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000810

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.86 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	0.24	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.81	ChemAxon
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	58.4 m³·mol⁻¹	ChemAxon
Polarizability	23.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	149.674	31661259
DarkChem	[M-H]-	147.717	31661259
DeepCCS	[M+H]+	151.217	30932474
DeepCCS	[M-H]-	148.859	30932474
DeepCCS	[M-2H]-	182.867	30932474
DeepCCS	[M+Na]+	157.558	30932474
AllCCS	[M+H]+	149.6	32859911
AllCCS	[M+H-H2O]+	145.8	32859911
AllCCS	[M+NH4]+	153.2	32859911
AllCCS	[M+Na]+	154.2	32859911
AllCCS	[M-H]-	150.2	32859911
AllCCS	[M+Na-2H]-	151.0	32859911
AllCCS	[M+HCOO]-	151.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoproterenol	CC(C)NCC(O)C1=CC(O)=C(O)C=C1	3281.4	Standard polar	33892256
Isoproterenol	CC(C)NCC(O)C1=CC(O)=C(O)C=C1	1764.1	Standard non polar	33892256
Isoproterenol	CC(C)NCC(O)C1=CC(O)=C(O)C=C1	1960.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoproterenol,1TMS,isomer #1	CC(C)NCC(O[Si](C)(C)C)C1=CC=C(O)C(O)=C1	1952.2	Semi standard non polar	33892256
Isoproterenol,1TMS,isomer #2	CC(C)NCC(O)C1=CC=C(O)C(O[Si](C)(C)C)=C1	1936.5	Semi standard non polar	33892256
Isoproterenol,1TMS,isomer #3	CC(C)NCC(O)C1=CC=C(O[Si](C)(C)C)C(O)=C1	1939.4	Semi standard non polar	33892256
Isoproterenol,1TMS,isomer #4	CC(C)N(CC(O)C1=CC=C(O)C(O)=C1)[Si](C)(C)C	2097.3	Semi standard non polar	33892256
Isoproterenol,2TMS,isomer #1	CC(C)NCC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1	1831.7	Semi standard non polar	33892256
Isoproterenol,2TMS,isomer #2	CC(C)NCC(O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1	1834.0	Semi standard non polar	33892256
Isoproterenol,2TMS,isomer #3	CC(C)N(CC(O[Si](C)(C)C)C1=CC=C(O)C(O)=C1)[Si](C)(C)C	2095.9	Semi standard non polar	33892256
Isoproterenol,2TMS,isomer #4	CC(C)NCC(O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1964.9	Semi standard non polar	33892256
Isoproterenol,2TMS,isomer #5	CC(C)N(CC(O)C1=CC=C(O)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2038.0	Semi standard non polar	33892256
Isoproterenol,2TMS,isomer #6	CC(C)N(CC(O)C1=CC=C(O[Si](C)(C)C)C(O)=C1)[Si](C)(C)C	2044.5	Semi standard non polar	33892256
Isoproterenol,3TMS,isomer #1	CC(C)NCC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1873.9	Semi standard non polar	33892256
Isoproterenol,3TMS,isomer #2	CC(C)N(CC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1)[Si](C)(C)C	2054.8	Semi standard non polar	33892256
Isoproterenol,3TMS,isomer #3	CC(C)N(CC(O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2053.3	Semi standard non polar	33892256
Isoproterenol,3TMS,isomer #4	CC(C)N(CC(O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2084.3	Semi standard non polar	33892256
Isoproterenol,4TMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2124.0	Semi standard non polar	33892256
Isoproterenol,4TMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2097.7	Standard non polar	33892256
Isoproterenol,4TMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2047.3	Standard polar	33892256
Isoproterenol,1TBDMS,isomer #1	CC(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C1	2180.8	Semi standard non polar	33892256
Isoproterenol,1TBDMS,isomer #2	CC(C)NCC(O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2187.9	Semi standard non polar	33892256
Isoproterenol,1TBDMS,isomer #3	CC(C)NCC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2196.1	Semi standard non polar	33892256
Isoproterenol,1TBDMS,isomer #4	CC(C)N(CC(O)C1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C	2351.7	Semi standard non polar	33892256
Isoproterenol,2TBDMS,isomer #1	CC(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2336.5	Semi standard non polar	33892256
Isoproterenol,2TBDMS,isomer #2	CC(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2344.3	Semi standard non polar	33892256
Isoproterenol,2TBDMS,isomer #3	CC(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C	2596.5	Semi standard non polar	33892256
Isoproterenol,2TBDMS,isomer #4	CC(C)NCC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2466.9	Semi standard non polar	33892256
Isoproterenol,2TBDMS,isomer #5	CC(C)N(CC(O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2562.2	Semi standard non polar	33892256
Isoproterenol,2TBDMS,isomer #6	CC(C)N(CC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[Si](C)(C)C(C)(C)C	2584.3	Semi standard non polar	33892256
Isoproterenol,3TBDMS,isomer #1	CC(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2593.4	Semi standard non polar	33892256
Isoproterenol,3TBDMS,isomer #2	CC(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[Si](C)(C)C(C)(C)C	2770.3	Semi standard non polar	33892256
Isoproterenol,3TBDMS,isomer #3	CC(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2761.8	Semi standard non polar	33892256
Isoproterenol,3TBDMS,isomer #4	CC(C)N(CC(O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2826.9	Semi standard non polar	33892256
Isoproterenol,4TBDMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2992.4	Semi standard non polar	33892256
Isoproterenol,4TBDMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2847.5	Standard non polar	33892256
Isoproterenol,4TBDMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2501.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05gr-9700000000-1d8ddbb3b9ecf4bd4e41	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (3 TMS) - 70eV, Positive	splash10-001i-4193300000-51704909fccedbd3a27f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoproterenol GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoproterenol 10V, Positive-QTOF	splash10-01ox-0940000000-a69543d0053d7699ab89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoproterenol 20V, Positive-QTOF	splash10-0udu-0900000000-6d817d647f12c2387c5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoproterenol 40V, Positive-QTOF	splash10-0zg3-7900000000-4048df303bf76bdeb169	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoproterenol 10V, Negative-QTOF	splash10-03di-1390000000-f9a4d1db36e6a6829da6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoproterenol 20V, Negative-QTOF	splash10-08fu-4940000000-b4ce8517db087019ae02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoproterenol 40V, Negative-QTOF	splash10-0a4i-8900000000-70b5626c51c5c776cac0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoproterenol 10V, Positive-QTOF	splash10-0006-0920000000-cf36ef242942ec87ce21	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoproterenol 20V, Positive-QTOF	splash10-0udi-4900000000-5b84f5f51437a459c629	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoproterenol 40V, Positive-QTOF	splash10-0k9j-8900000000-1d0384f1f487a005b30c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoproterenol 10V, Negative-QTOF	splash10-03di-0090000000-840d7dbcf79278e91a76	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoproterenol 20V, Negative-QTOF	splash10-01w0-0910000000-545a4d1a8047f492d874	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoproterenol 40V, Negative-QTOF	splash10-0a4u-5900000000-5b03f3b94e0d996de579	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Isoprenaline Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01064	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01064	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01064

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3647

KEGG Compound ID

C07056

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoprenaline

METLIN ID

Not Available

PubChem Compound

3779

PDB ID

Not Available

ChEBI ID

64317

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Mitogen-activated protein kinase 1

General function:: Involved in MAP kinase activity
Specific function:: Acts as a transcriptional repressor. Binds to a [GC]AAA[GC] consensus sequence. Repress the expression of interferon gamma-induced genes. Seems to bind to the promoter of CCL5, DMP1, IFIH1, IFITM1, IRF7, IRF9, LAMP3, OAS1, OAS2, OAS3 and STAT1. Transcriptional activity is independent of kinase activity
Gene Name:: MAPK1
Uniprot ID:: P28482
Molecular weight:: 41389.3

References

Vaniotis G, Del Duca D, Trieu P, Rohlicek CV, Hebert TE, Allen BG: Nuclear beta-adrenergic receptors modulate gene expression in adult rat heart. Cell Signal. 2011 Jan;23(1):89-98. doi: 10.1016/j.cellsig.2010.08.007. Epub 2010 Aug 21. [PubMed:20732414 ]
Oudit GY, Crackower MA, Eriksson U, Sarao R, Kozieradzki I, Sasaki T, Irie-Sasaki J, Gidrewicz D, Rybin VO, Wada T, Steinberg SF, Backx PH, Penninger JM: Phosphoinositide 3-kinase gamma-deficient mice are protected from isoproterenol-induced heart failure. Circulation. 2003 Oct 28;108(17):2147-52. Epub 2003 Sep 8. [PubMed:12963636 ]
Azzi M, Charest PG, Angers S, Rousseau G, Kohout T, Bouvier M, Pineyro G: Beta-arrestin-mediated activation of MAPK by inverse agonists reveals distinct active conformations for G protein-coupled receptors. Proc Natl Acad Sci U S A. 2003 Sep 30;100(20):11406-11. Epub 2003 Sep 17. [PubMed:13679574 ]
Adissu HA, Schuller HM: Antagonistic growth regulation of cell lines derived from human lung adenocarcinomas of Clara cell and aveolar type II cell lineage: Implications for chemoprevention. Int J Oncol. 2004 Jun;24(6):1467-72. [PubMed:15138589 ]
Dubey RK, Jackson EK, Gillespie DG, Zacharia LC, Imthurn B: Catecholamines block the antimitogenic effect of estradiol on human coronary artery smooth muscle cells. J Clin Endocrinol Metab. 2004 Aug;89(8):3922-31. [PubMed:15292328 ]
Yeh CK, Ghosh PM, Dang H, Liu Q, Lin AL, Zhang BX, Katz MS: beta-Adrenergic-responsive activation of extracellular signal-regulated protein kinases in salivary cells: role of epidermal growth factor receptor and cAMP. Am J Physiol Cell Physiol. 2005 Jun;288(6):C1357-66. Epub 2005 Feb 2. [PubMed:15689414 ]

Enzyme Details

2. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Beta-1 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:: ADRB1
Uniprot ID:: P08588
Molecular weight:: 51322.1

References

Sato M, Gong H, Terracciano CM, Ranu H, Harding SE: Loss of beta-adrenoceptor response in myocytes overexpressing the Na+/Ca(2+)-exchanger. J Mol Cell Cardiol. 2004 Jan;36(1):43-8. [PubMed:14734046 ]
Jurgens CW, Rau KE, Knudson CA, King JD, Carr PA, Porter JE, Doze VA: Beta1 adrenergic receptor-mediated enhancement of hippocampal CA3 network activity. J Pharmacol Exp Ther. 2005 Aug;314(2):552-60. Epub 2005 May 20. [PubMed:15908512 ]
Kobayashi H, Narita Y, Nishida M, Kurose H: Beta-arrestin2 enhances beta2-adrenergic receptor-mediated nuclear translocation of ERK. Cell Signal. 2005 Oct;17(10):1248-53. Epub 2005 Feb 12. [PubMed:16038799 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Ahlquist RP: Present state of alpha- and beta-adrenergic drugs I. The adrenergic receptor. Am Heart J. 1976 Nov;92(5):661-4. [PubMed:10722 ]

Enzyme Details

4. Beta-2 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:: ADRB2
Uniprot ID:: P07550
Molecular weight:: 46458.3

References

Abraham G, Kottke C, Dhein S, Ungemach FR: Pharmacological and biochemical characterization of the beta-adrenergic signal transduction pathway in different segments of the respiratory tract. Biochem Pharmacol. 2003 Sep 15;66(6):1067-81. [PubMed:12963495 ]
Jones SM, Hiller FC, Jacobi SE, Foreman SK, Pittman LM, Cornett LE: Enhanced beta2-adrenergic receptor (beta2AR) signaling by adeno-associated viral (AAV)-mediated gene transfer. BMC Pharmacol. 2003 Dec 4;3:15. [PubMed:14656380 ]
Teixeira CE, Baracat JS, Zanesco A, Antunes E, De Nucci G: Atypical beta-adrenoceptor subtypes mediate relaxations of rabbit corpus cavernosum. J Pharmacol Exp Ther. 2004 May;309(2):587-93. Epub 2004 Jan 29. [PubMed:14752060 ]
Odley A, Hahn HS, Lynch RA, Marreez Y, Osinska H, Robbins J, Dorn GW 2nd: Regulation of cardiac contractility by Rab4-modulated beta2-adrenergic receptor recycling. Proc Natl Acad Sci U S A. 2004 May 4;101(18):7082-7. Epub 2004 Apr 22. [PubMed:15105445 ]
Uezono Y, Kaibara M, Murasaki O, Taniyama K: Involvement of G protein betagamma-subunits in diverse signaling induced by G(i/o)-coupled receptors: study using the Xenopus oocyte expression system. Am J Physiol Cell Physiol. 2004 Oct;287(4):C885-94. Epub 2004 May 19. [PubMed:15151902 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Ahlquist RP: Present state of alpha- and beta-adrenergic drugs I. The adrenergic receptor. Am Heart J. 1976 Nov;92(5):661-4. [PubMed:10722 ]

Enzyme Details

5. Phosphatidylinositol 3-kinase regulatory subunit alpha

General function:: Involved in phosphoinositide 3-kinase regulator activity
Specific function:: Binds to activated (phosphorylated) protein-Tyr kinases, through its SH2 domain, and acts as an adapter, mediating the association of the p110 catalytic unit to the plasma membrane. Necessary for the insulin-stimulated increase in glucose uptake and glycogen synthesis in insulin-sensitive tissues
Gene Name:: PIK3R1
Uniprot ID:: P27986
Molecular weight:: 83597.7

References

Slomiany BL, Slomiany A: Salivary phospholipid secretion in response to beta-adrenergic stimulation is mediated by Src kinase-dependent epidermal growth factor receptor transactivation. Biochem Biophys Res Commun. 2004 May 21;318(1):247-52. [PubMed:15110780 ]
Slomiany BL, Slomiany A: Secretion of gastric mucus phospholipids in response to beta-adrenergic G protein-coupled receptor activation is mediated by SRC kinase-dependent epidermal growth factor receptor transactivation. J Physiol Pharmacol. 2004 Sep;55(3):627-38. [PubMed:15381832 ]
Slomiany BL, Slomiany A: Src-kinase-dependent epidermal growth factor receptor transactivation in salivary mucin secretion in response to beta-adrenergic G-protein-coupled receptor activation. Inflammopharmacology. 2004;12(3):233-45. [PubMed:15527548 ]
Machida K, Inoue H, Matsumoto K, Tsuda M, Fukuyama S, Koto H, Aizawa H, Kureishi Y, Hara N, Nakanishi Y: Activation of PI3K-Akt pathway mediates antiapoptotic effects of beta-adrenergic agonist in airway eosinophils. Am J Physiol Lung Cell Mol Physiol. 2005 May;288(5):L860-7. Epub 2004 Dec 23. [PubMed:15618457 ]
Slomiany BL, Slomiany A: Gastric mucin secretion in response to beta-adrenergic G protein-coupled receptor activation is mediated by SRC kinase-dependent epidermal growth factor receptor transactivation. J Physiol Pharmacol. 2005 Jun;56(2):247-58. [PubMed:15985706 ]

Enzyme Details

6. Phosphatidylinositol 3-kinase regulatory subunit gamma

General function:: Involved in phosphoinositide 3-kinase regulator activity
Specific function:: Binds to activated (phosphorylated) protein-tyrosine kinases through its SH2 domain and regulates their kinase activity. During insulin stimulation, it also binds to IRS-1
Gene Name:: PIK3R3
Uniprot ID:: Q92569
Molecular weight:: 54462.1

References

Slomiany BL, Slomiany A: Salivary phospholipid secretion in response to beta-adrenergic stimulation is mediated by Src kinase-dependent epidermal growth factor receptor transactivation. Biochem Biophys Res Commun. 2004 May 21;318(1):247-52. [PubMed:15110780 ]
Slomiany BL, Slomiany A: Secretion of gastric mucus phospholipids in response to beta-adrenergic G protein-coupled receptor activation is mediated by SRC kinase-dependent epidermal growth factor receptor transactivation. J Physiol Pharmacol. 2004 Sep;55(3):627-38. [PubMed:15381832 ]
Slomiany BL, Slomiany A: Src-kinase-dependent epidermal growth factor receptor transactivation in salivary mucin secretion in response to beta-adrenergic G-protein-coupled receptor activation. Inflammopharmacology. 2004;12(3):233-45. [PubMed:15527548 ]
Machida K, Inoue H, Matsumoto K, Tsuda M, Fukuyama S, Koto H, Aizawa H, Kureishi Y, Hara N, Nakanishi Y: Activation of PI3K-Akt pathway mediates antiapoptotic effects of beta-adrenergic agonist in airway eosinophils. Am J Physiol Lung Cell Mol Physiol. 2005 May;288(5):L860-7. Epub 2004 Dec 23. [PubMed:15618457 ]
Slomiany BL, Slomiany A: Gastric mucin secretion in response to beta-adrenergic G protein-coupled receptor activation is mediated by SRC kinase-dependent epidermal growth factor receptor transactivation. J Physiol Pharmacol. 2005 Jun;56(2):247-58. [PubMed:15985706 ]

Enzyme Details

7. Phosphatidylinositol 3-kinase regulatory subunit beta

General function:: Involved in phosphoinositide 3-kinase regulator activity
Specific function:: Binds to activated (phosphorylated) protein-tyrosine kinases, through its SH2 domain, and acts as an adapter, mediating the association of the p110 catalytic unit to the plasma membrane
Gene Name:: PIK3R2
Uniprot ID:: O00459
Molecular weight:: 81623.7

References

Slomiany BL, Slomiany A: Salivary phospholipid secretion in response to beta-adrenergic stimulation is mediated by Src kinase-dependent epidermal growth factor receptor transactivation. Biochem Biophys Res Commun. 2004 May 21;318(1):247-52. [PubMed:15110780 ]
Slomiany BL, Slomiany A: Secretion of gastric mucus phospholipids in response to beta-adrenergic G protein-coupled receptor activation is mediated by SRC kinase-dependent epidermal growth factor receptor transactivation. J Physiol Pharmacol. 2004 Sep;55(3):627-38. [PubMed:15381832 ]
Slomiany BL, Slomiany A: Src-kinase-dependent epidermal growth factor receptor transactivation in salivary mucin secretion in response to beta-adrenergic G-protein-coupled receptor activation. Inflammopharmacology. 2004;12(3):233-45. [PubMed:15527548 ]
Machida K, Inoue H, Matsumoto K, Tsuda M, Fukuyama S, Koto H, Aizawa H, Kureishi Y, Hara N, Nakanishi Y: Activation of PI3K-Akt pathway mediates antiapoptotic effects of beta-adrenergic agonist in airway eosinophils. Am J Physiol Lung Cell Mol Physiol. 2005 May;288(5):L860-7. Epub 2004 Dec 23. [PubMed:15618457 ]
Slomiany BL, Slomiany A: Gastric mucin secretion in response to beta-adrenergic G protein-coupled receptor activation is mediated by SRC kinase-dependent epidermal growth factor receptor transactivation. J Physiol Pharmacol. 2005 Jun;56(2):247-58. [PubMed:15985706 ]

Enzyme Details

8. Beta-3 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis
Gene Name:: ADRB3
Uniprot ID:: P13945
Molecular weight:: 43518.6

References

Ahlquist RP: Present state of alpha- and beta-adrenergic drugs I. The adrenergic receptor. Am Heart J. 1976 Nov;92(5):661-4. [PubMed:10722 ]
Schiffelers SL, Blaak EE, Saris WH, van Baak MA: In vivo beta3-adrenergic stimulation of human thermogenesis and lipid use. Clin Pharmacol Ther. 2000 May;67(5):558-66. [PubMed:10824635 ]

Showing metabocard for Isoproterenol (HMDB0015197)

MOL for HMDB0015197 (Isoproterenol)

3D MOL for HMDB0015197 (Isoproterenol)

3D SDF for HMDB0015197 (Isoproterenol)

3D-SDF for HMDB0015197 (Isoproterenol)

PDB for HMDB0015197 (Isoproterenol)

3D PDB for HMDB0015197 (Isoproterenol)

SMILES for HMDB0015197 (Isoproterenol)

INCHI for HMDB0015197 (Isoproterenol)

Structure for HMDB0015197 (Isoproterenol)

3D Structure for HMDB0015197 (Isoproterenol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

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References